How (and Why) to Throw a Kick-ass Company Retreat

Ben Lerer is a managing director at Lerer Ventures and the co-founder and CEO of Thrillist Media Group, a digital media company converging leading men's lifestyle brand Thrillist.com, and members-only shopping club JackThreads.com. Lerer also chairs the Board of Directors for the East River Development Alliance, a New York non-profit organization.

co-founder and CEO

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Our first company retreat was just three employees and myself going to the park and having a catch. Needless to say, that was not a good one. Now, I think we've figured it out.

I've found that the No. 1 thing that leads to people being happy at work is transparency, so at our retreats, transparency is our focus.

This year, we created breakout sessions to educate people about what's going on at other parts of the company. When people are working their butts off, it's easy to say, "My job is so tough. Why is yours so easy?" The idea of these sessions was to A. educate people and B. make them appreciate how hard everyone around them is working.

The whole company voted for sessions they wanted to attend, and we narrowed it down to five. For one, we had our ad sales lead talk about what a salesperson's job really entails, which helped dispel the stereotype that sales people are just wining and dining people.

Another piece of advice: Spend money. I don't mean waste money. But the team will appreciate it if you don't cheap out. If employees feel like you're really investing in them, they'll invest back. And don't do it in one day. Make it two. Make it a big deal, and give people time to let their guard down.

Lastly, take time to make people feel the warm and fuzzies. When we were smaller, I would give a speech and talk about every employee, one by one. Now, I talk about each team. At the end of each speech, the whole company gives that team a standing ovation. It's a real pump-up. If you make people proud of the work they're doing, that pride will reflect in high-quality work in the future.